


Old Dog, New Tricks

by guilty_pleasures_abound



Category: Gravity Falls
Genre: Anal Fingering, Blow Jobs, Dildos, Established Relationship, F/M, Fingerfucking, Hand Jobs, POV Female Character, POV Second Person, Pegging, Strap-Ons
Language: English
Status: Completed
Published: 2019-08-21
Updated: 2019-08-21
Packaged: 2020-09-23 16:50:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,530
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20343436
Author URL: https://archiveofourown.org/users/guilty_pleasures_abound/pseuds/guilty_pleasures_abound
Summary: They say you can’t teach an old dog new tricks, but when it came to the old dog known as Stanley Pines, you were determined to prove that saying wrong.[Female reader]





	Old Dog, New Tricks

**Author's Note:**

> ::COUGH::thismayormaynotbeinspiredbymyreallifeexperiences::COUGH::

They say you can’t teach an old dog new tricks, but when it came to the old dog known as Stanley Pines, you were determined to prove that saying wrong.

“You wanna do _what_ now?” he asked the first time you’d brought it up, his bushy eyebrows shooting straight up into his hairline.

“Pegging,” you’d stated again, easy as you please, almost flippant; it was an effort to make it sound casual, instill the idea that it really wasn’t as big of a deal as he was going to try to make it into. “I’ve let you fuck my ass, why shouldn’t we do it the other way around?”

His face was as red as a tomato, his mouth opening and closing several times as he tried to figure out what to say to that.

“Because!” he eventually stuttered. “I’m… I’m not—!”

“What, not into the idea of having a more intense orgasm thanks to prostate stimulation?” You raised an eyebrow at him.

His face got redder, his arms crossed in front of his chest.

“Broaden your horizons, my love,” you’d said next, moving close to kiss him on the nose and pet his hair. “You might surprise yourself with what you end up liking.”

You didn’t bring it up again, simply leaving Stan to ruminate on it.

You began to suspect he was playing around with the concept by himself when you found the lube in the shower instead of its usual place in the bedside table drawer. You also couldn't deny your giddy little smile, leaving the lube where it was so as not to alert him to the fact that you knew, but most definitely enjoying the mental fantasy of him jerking off with his fingers in his ass, exploring and experimenting with himself in a way he hadn't before.

"This whole... pegging idea of yours," he said a couple months later, petting your hair where you were laying with your head on his chest. "This isn't some weird fetish where you want to see me get fucked with like... a fake horse dick or something, is it?"

You couldn't help but chortle, combing your fingers through his ample chest hair. "Nah. I'd do it if it was something you were into, but it's not something I'm aiming for."

He grunted in acknowledgement. "What are you aiming for, then?"

"You know the pink one?"

He was very familiar with "the pink one;" a nice little dildo with an upward curve and a bulbous head—perfect for both your g-spot stimulation and hopefully just as nice for his prostate. There was the added benefit of it being a rather modest size, only about five inches of insertable length and roughly an inch wide. Perfectly unintimidating, you felt, which was probably why he didn't mind using it while he had his tongue on your clit.

He gave a contemplative hum, fingertips moving to dance along your shoulder.

“I’ll… I’ll think about it,” he said.

The fact that he _was_ thinking about it was a victory all on its own, and you smiled, tucking it into a kiss against his chest.

"We can start small," you still reminded him, "Just fingers, if you want."

He hummed again, but you heard his throat swallow audibly. "We... we can. Do fingers."

He _definitely_ was experimenting on his own, if he was going to allow you to do it, which was such a deep thrill that you didn't even try to suppress your impulse to squeeze your arm tightly around his middle with a big smile.

"Alright, easy tiger," he chuffed. "We're not doing it _now_."

"I know, just... thanks. For trusting me."

You knew without looking that he was blushing, so you gave him another squeeze before sitting up to give him a kiss too, bringing your hand up to pet over his hair gently.

"Yeah, well..." he mumbled against your lips. "Just don't be weird about it, alright?"

"I promise."

And honestly, you did your best, but when you were giving him a lazy morning blowjob a few days later and he momentarily stopped you to hand you the lube and mutter a gruff, “You can… do the thing.” it was hard not to be a little bit giddy.

“Don’t be weird about it,” he insisted again as you sat back with a wide grin, hooking your hands under his knees and drawing them up, planting his feet flat on the bed as his face blushed a rather intense red.

“I’m not!” you murmured, leaning over him to kiss your way up his belly and chest until you reached his face, kissing his mouth with a soft hum. “I’m not, I promise.”

He “harrumph”ed, his hands going to your chest and giving your breasts a squeeze before you sat back again, opening the lube bottle to put a healthy squirt on your fingertips. Then it was back to having your mouth around his cock, doing your best to distract him from his obvious nervousness as you rubbed your fingers with your thumb, spreading the slippery lube around more evenly. The distraction seemed to work, his breath sighing out on a little moan and his hands petting over your hair as you rigorously rubbed your tongue over the tip of his cock, the suction of your mouth tight, your lube-free hand squeezing and stroking along the rest of his shaft, wet with spit.

He shivered when you rubbed the back of your knuckles against his perineum, but didn’t pull away, or jump from the contact, instead letting out a long breath and leaning his knees out even further. It was permission and encouragement, bringing a satisfied little hum from your throat as you dipped your fingers further back.

Familiarity was such a funny thing; it almost made you forget, sometimes, how Stan’s grey body hair covered his skin so amply, thick down here just as it was everywhere else. Still, it wasn't difficult to find his hole, petting your finger against it with slow, broad strokes. It made the muscles in his thighs twitch, his breath catching.

You raised your head, your hand still stroking along his cock and fingers rubbing gentle circles against his asshole. "You sure you're good?"

"M'good," he grunted.

"If you want me to stop—"

"I'll tell you, now get back to it, will ya?"

You gave a little chortle, twisting your grip at the tip of his cock just to feel him twitch. "Damn, demanding already. Should have known you'd turn into a pillow princess."

You'd never seen his face turn so scarlet, the color spreading to his ears and down his chest delightfully, but you ducked your head back down before he could find any words for a snappy comeback. You had to confess was kinda cute, getting him flustered.

You also readily confessed that _this_ was always sexy—going down on him, feeling him twitch in your mouth, hearing him huff and groan as you rubbed your tongue against the head of his cock before pressing lower, taking him deeper with a fluttery swallow.

Pressing your fingers against his asshole made it even hotter than usual, the little ring of muscle fluttering and spasming against the rub and press, seemingly torn on whether to welcome the intrusion or not. You, in turn, didn't rush it; sucking his cock slow and steady, warming his body up to the idea with a gentle touch.

"Fuckin'—!" He gasped a small eon later, his hands reaching for your head and his legs shifting restlessly against the bed, still splayed open and twitching at the stimulation.

You took it as a nudge to stop the teasing touch, finally sinking the tip of one finger inside him, the muscles fluttering but not seizing; exactly the reception you'd been working toward.

"Shit," he gasped, but he didn't sound distressed; it was exactly the same sexy, breathless cursing he gave you when you climbed astride his lap and sank down on his cock, or when you took as much of him into the back of your throat as you could. It was the kind of breathless cursing that told you Stan was very, _very_ turned on.

You dared to press a little deeper, a little surprised but most certainly pleased when you encountered practically no resistance.

_You cheeky slut,_ you thought with amusement, shallow thrusting of your finger making his thighs tremble on either side of you. _Knew you'd like this if you just gave it a chance._

It wasn't until you were buried to the last knuckle that you pulled your mouth off his cock, swallowing as you lifted your head to look at him. He was absolutely pink from forehead to chest, his hands sliding from your head to grip the sheets on either side of him as he squirmed restlessly under your gaze.

"Alright?" you asked him.

"Yeah," he breathed.

"Think you can handle another?"

His throat clicked as he swallowed, his cock twitching, his length flushed a deep red and shiny with spit, a pearl of precum beading at the tip.

"Yeah," he eventually answered.

You reapplied the lube to your fingers, taking him at his word and watching his face this time as you pressed the tip of your second finger in along with your first. He bit his lip, the fine tremors in his thighs becoming more noticeable but his erection not flagging in the slightest.

It made it all the more satisfying when you angled your fingers inside him just right, his whole body jolting with a gasp that made you suddenly vividly aware of how much you were aching between your legs, how absolutely, _astonishingly_ hot it was to have him as your mercy like this.

"What the _fuck_—" he gasped when you did it again, the beginning of a slow rhythm that immediately turned him into a shivering, twitching mess before your very eyes.

God, it was so hot, you almost couldn't believe you were getting to see this; Stan's cock twitching in your hand with every rock of your fingers against his prostate, his stuttering breath, his flushed skin.

"You gonna come for me if I suck your cock again, honey?" you asked him, biting your lip at his answering moan.

"God, please," he rasped, writhing with another moan that made you throb. "Fuck, baby, please, I'm gonna fucking die."

You absolutely couldn't refuse such a deliciously sexy plea, taking him deep into your mouth as you sucked hard; riding that line of too much, almost enough to make you choke and gag while your fingers thrust firmly against that sweet spot inside him.

He actually cried out when he came, thick spurts of his load hitting the back of your mouth and his whole body jerking like you had shocked him with electricity.

"Fuck fuck _fuuuuuck_," he groaned, big hand gripping your shoulder and another pulse of cum flooding your mouth until you swallowed with a low moan. "God, stop, I can't—"

You pulled off, sliding your fingers slowly and gently from his ass to give him space to breathe, watching his chest heave and his legs twitch with aftershocks.

You wiped the back of your hand across your mouth, shuffling forward to place a line of kisses along his abdomen and up his chest, his hands coming up to pet over you weakly.

"Not bad, huh?" you murmured, making your way up until you were leaning over him on all fours, face pressed close to his, brushing your noses together gently before angling in for a soft kiss.

"I... didn't expect it to be like that," he whispered. "That was... good."

You couldn't help but smile, another soft kiss pressed against his lips. "Good enough for a repeat performance in the future?"

He nodded wordlessly, his hand cradling the back of your head, his fingers rubbing gently against your scalp.

"Wanna watch me get off?" you murmured next, tilting your head back enough to give him a little grin. "That was fucking _hot_."

He looked bashfully pleased, pulling you back in for another kiss.

"Give me a minute to catch my breath and you can sit on my face," he offered instead; a much better deal in your book.

"Let me wash my hands and I'll take you up on that."

He guffawed, watching you sit back with amusement. "Hurry up, babydoll."

***

You liked Stan’s back; it really made you appreciate just how broad his torso was. Broad and hairy—that was Stan in a nutshell, and you wouldn’t have it any other way.

In this particular circumstance, it was particularly sexy; Stan laying on his belly on the bed, that broad back easily available for you to run your hands over, his hips hitched up a little by the pillow tucked under them. A pillow that would be in desperate need of a wash by the time you were done, if you had anything to say about it.

You absentmindedly stroked the nice pink dildo on the front of your strap-on harness, spreading the healthy amount of lube on it around a little more.

“God you’re sexy,” you couldn’t help but mutter, your free hand splayed wide against his back, dragging it down his spine with firm pressure from top to tailbone. “You’re so sexy and I get to fuck you, what a fucking dream.”

He gave a quiet chortle, twisting slightly to look back at you. “You ain’t gotta flatter me, toots, I’ve already said you can do this.”

You laughed, giving his asscheek a little smack that made him gasp. “I know! Can’t I compliment you just for the hell of it?”

That roguish grin you loved so much flashed across his face. "You'd better. I'm a damn catch, you know."

You laughed as you smacked his ass again, then gave a little pinch, his resulting squirm and huff amusing you. "And so humble, too."

"Humble-shmumble, I never got nothing from being humble."

You chortled, shaking your head as you shuffled closer on the mattress, one hand petting over his back as the other guided the dildo between his cheeks, rubbing the bulbous head against his lube-slick hole.

He let his cheek rest back down on the bed with a shaky breath, hands pressed flat against the mattress on either side of his head.

"You good?" you asked.

"I'm great, baby."

That’s what you loved to hear.

You leaned forward, guiding the strap-on against him and beginning the slow slide in, your other hand in the middle of his back, and your gaze flicking between the press of the fake dick into his body and what you could see of the side of his face. You saw him grimace a bit, the fat head stretching him a little uncomfortably, but once the widest part was through that ring of muscle, it was almost too easy to slide the rest of the way in.

He shuddered when your hips met his ass, and you could tell from the fluttering little twitch of his hole that he was reflexively clenching around it; fuck, you couldn’t help but wish the strap-on between your legs was real—that you could feel him reacting to the penetration the way he could when he was inside you.

You withdrew a little, slow and gentle, then canted your hips back in to the sound of him panting out a soft groan.

“Good?” you asked.

“Good,” he echoed, his voice even raspier than usual, filling you with satisfaction.

It was a struggle to keep it slow, to keep the rock of your hips gentle as you started building rhythm, fingers of one hand curled around the side of his hip and the other still on his back, sliding up and down his spine and watching the stiff pink length between your legs sink inside him.

It was fucking _hypnotizing_, is what it was. You could feel your cunt throbbing, heat spreading over your chest, your mouth hanging open slightly as you panted. God, you thought fingering him was hot, but _this?_ This was obscene, this was hotter than it had any right to be.

You leaned over him with a dreamy moan, pressing a trail of kisses along his scapula, along the edge of the burn that he trusted you enough to know the secret of, his skin hot and flushed, and you felt a literal gush of wetness between your legs when he gasped and groaned; jerking back into the deeper press of the dildo with a shudder.

“There,” he gasped with another groan, hitching back with a squirm and a shiver. “Right fucking there, _fuck_.”

It was a demand you could never imagine refusing, keeping the angle of your hips steady as you started to move with more purpose, more force, the impact getting hard enough to jolt the back of the dildo against your clit through the harness.

"Oh my _god_." His cheeks were so pink, his mouth open and panting, the dampness of sweat starting to make his skin tacky. He was completely into this, you just knew if you slid a hand under his hips you'd find him stiff and leaking precum onto the pillow.

"Good boy." The words slipped out of your mouth in a reverent whisper, smeared across the skin of his back. "So good, Stan, fucking love you like this."

His moan edged into a whimper, his whole-body shudder and writhe making your pussy throb furiously, slickness literally slipping down your legs as you helplessly ground forward in answer, desperate for any pressure on your clit to alleviate the most intense arousal of your life.

You knew it would be hot, you knew that if Stan let you do this you would have the memory forever seared into your brain, it would have a place of honor in your spank bank for as long as you lived. But the level of turned-on you were feeling, how amped up and close to climax you already were just from this...

Your lust-liquified brain needed a moment to catch up when Stan suddenly reached for your hand where you were still gripping his waist, lifting his hips just enough to pull it under him and wrap it around his cock. His gasp of relief jolted you into action, wrapping your fingers tighter around him like he so clearly wanted you to do.

"You gonna come for me?" you whispered, his precum-wet cockhead rubbing intently against your palm as you kept on pumping your hips. "You gonna come on my cock, honey?"

You didn't really expect an answer, nor did he give you one, but the hard twitch of his cock in your hand and his raspy moan was all the affirmation you needed. He was close, and eager to get there, and so were you.

You were a little bit selfish for a moment, you couldn’t help it; grinding in to put better pressure on your clit, your pussy spasming and squeezing desperately around nothing, the short strokes of your hand around his cock uneven and arrhythmic with your distraction. It was hard to refocus, your head in a daze and your body on edge, but when Stan writhed with a frustrated grunt, it helped to pull you out of the lustful fog filling up your head.

“Alright,” you murmured, mostly to yourself rather than to him, “alright, I’ve got you.”

You knew how he liked to be touched, you knew how tight to squeeze your hand, how to stroke him just right, so you did; matching the pace of your hips to the hand wrapped around his cock. It was a sudden synergy, Stan fast on the path of unraveling under you, and you watched with greedy desire as it happened.

He cried out when he came, dick spurting thick streams of spunk into your palm, one right after another, his hands fisted and teeth biting the bedding. It was _hot_, it was _so hot_, and this time you really couldn’t stop yourself from grinding against his ass, reaching so desperately for that last little bit of stimulation that would get you there too.

You squeaked when you found it, you couldn’t help it, warm heat spreading through your cunt and pleasure sliding through your nervous system. Under you Stan was gasping, squirming at the onslaught, but made no move to stop you.

“Fuck, did you just come?” He sounded dazed, amazed, spasming and shuddering as the final pulses of pleasure jolted through your pussy.

“Yeah,” was all you could pant, still a little amazed yourself.

“Fuck that’s so hot,” he moaned. “I can’t believe this turns you on that much.”

You chortled, laying a trail of messy kisses along his back as you slid your cum-covered hand out from under him. “Makes two of us.”

“Yeah, well…” he grumbled. You knew before you even looked up that his ears were red, flustered at how hard he had just come from something he hadn’t expected to like so much, especially when you pointed it out.

It made you smirk, pressing more kisses along his back. You couldn’t wait to see what else you could convince him to experiment with.

**Author's Note:**

> [Hey look I've got a Grunkle shrine.](https://guilty-pleasures-abound.tumblr.com/)


End file.
